Where to stay around South Side?

Our 2019 property listings offer a large selection of 1,002 vacation rentals near South Side. From 830 Condos/Apartments to 665 Studios, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near South Side for a holiday or a weekend are on HomeAway.

What are the most popular destinations to visit in South Side?

There are many lovely places to stay for a holiday trip or just for a weekend in South Side. From HomeAway travelers, the most popular destinations to visit are:

  • Indiana: 2,697 vacation rentals
  • Lake Michigan: 13,814 vacation rentals
  • Chicago Loop: 490 vacation rentals
  • Downtown Chicago: 998 vacation rentals
  • Lincoln Park: 604 vacation rentals

And HomeAway offers you the chance to discover many other popular destinations in South Side! Please use our search bar to access the selection of vacation rentals available in other popular destinations.

What are the main cities to discover in South Side?

Whether you're traveling with family or friends, here are the cities with the largest selection of vacation rentals for a holiday trip or just for a weekend in South Side:

  • Evanston: 1,278 rentals
  • Oak Park: 1,612 rentals
  • Rosemont: 214 rentals
  • Gary: 67 rentals
  • Tinley Park: 28 rentals

For other cities, please use our search bar to access the selection of vacation rentals available.

Can I find easy-access vacation rentals when traveling by plane to South Side?

Yes of course. Our owners offer a large selection of vacation rentals near airports. The airports with a large selection of vacation rentals in South Side are:

  • O'Hare International Airport (ORD): 2,825 vacation rentals
  • Chicago Midway International Airport (MDW): 2,219 vacation rentals
  • Gary Chicago International Airport (GYY): 186 vacation rentals

For other airports, please use our search bar to access the selection of vacation rentals available.